(R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-N,N-diethyl-acetamide → N,N-diethyl-2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}-acetamide

Participants

Reaction Steps

A solution of (R)-(pyridin-3-yl)oxirane (97 mg, 0.80 mmol) and (R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-N,N-diethylacetamide (243 mg, 0.80 mmol) in water (0.8 mL) and ethanol (8 mL) is refluxed for 5 hours. After concentrated, the resulting residue is purified by preparative TLC (SiO2, 20×20 cm, 0.5 mm, iPrOH/saturated ammonia solution in chloroform=1/10) to give the desired N,N-diethyl-2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}-acetamide (70 mg, yield: 21%).

Provenance & Evidence